Cefdinir

Identification

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Name

Cefdinir

Accession Number

DB00535  (APRD00644)

Type

Small Molecule

Groups

Approved

Description

Cefdinir, also known as Omnicef, is a semi-synthetic, broad-spectrum antibiotic belonging to the third generation of the cephalosporin class. It has been proven to be effective for the treatment of common bacterial infections in the ear, sinus, throat, lungs, and skin. Cefdinir was approved by the FDA in 1997 to treat a variety of mild to moderate infections and was initially marketed by Abbvie.^6,16 Because of its chemical structure, it is effective against organisms that are resistant to first-line cephalosporin therapy due to the production of beta-lactamase enzymes.^2,3

Structure

3D

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MOLSDF3D-SDFPDBSMILESInChI

Similar Structures

Structure for Cefdinir (DB00535)

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Synonyms

• (6R,7R,Z)-7-(2-(2-aminothiazol-4-yl)-2-(hydroxyimino)acetamido)-8-oxo-3-vinyl-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• (6R,7R)-7-{2-(2-Amino-thiazol-4-yl)-2-[(Z)-hydroxyimino]-acetylamino}-8-oxo-3-vinyl-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• Cefdinir
• Cefdinirum
• CFDN

External IDs

BMY-28488 / CI 983 / CI-983 / FK 482 / FK-482

Product Ingredients

Ingredient	UNII	CAS	InChI Key
Cefdinir monohydrate	6E7SN358SE	213978-34-8	QWUVJQSNISEEQI-KYIYMPJCSA-N

Product Images

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Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
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Omnicef	Powder, for suspension	125 mg/5mL	Oral	Abbvie	1997-12-04	2011-05-31
Omnicef	Capsule	300 mg/1	Oral	Abbvie	1997-12-04	2011-05-31
Omnicef	Powder, for suspension	250 mg/5mL	Oral	Physicians Total Care, Inc.	1997-12-04	2012-06-30
Omnicef	Powder, for suspension	250 mg/5mL	Oral	Abbvie	1997-12-04	2011-05-31

Additional Data Available

Application Number
Application Number
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Product Code
Product Code
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Generic Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
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Cefdinir	Powder, for suspension	250 mg/5mL	Oral	A-S Medication Solutions	2007-05-08	Not applicable
Cefdinir	Capsule	300 mg/1	Oral	Avera McKennan Hospital	2016-05-19	2018-07-09
Cefdinir	Capsule	300 mg/1	Oral	OrchidPharma Inc	2014-07-04	2019-12-31
Cefdinir	Powder, for suspension	250 mg/5mL	Oral	Preferred Pharmaceuticals Inc.	2018-09-14	Not applicable
Cefdinir	Capsule	300 mg/1	Oral	Rebel Distributors	2011-01-14	Not applicable
Cefdinir	Capsule	300 mg/1	Oral	Rebel Distributors	2008-01-07	Not applicable
Cefdinir	Powder, for suspension	250 mg/5mL	Oral	Sandoz	2007-04-06	Not applicable
Cefdinir	Powder, for suspension	250 mg/5mL	Oral	Par Pharmaceutical	2014-05-01	2017-09-30
Cefdinir	Capsule	300 mg/1	Oral	PD-Rx Pharmaceuticals, Inc.	2007-04-06	Not applicable
Cefdinir	Powder, for suspension	250 mg/5mL	Oral	REMEDYREPACK INC.	2019-05-13	Not applicable

Additional Data Available

Application Number
Application Number
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Product Code
Product Code
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International/Other Brands

Cednir (Abbott) / Cefdiel (Ranbaxy) / Cefzon (Astellas) / Duocef (Ranbaxy) / Efdinir (Incepta) / Idinir (Invision) / Kefnir (Glenmark) / Nirocef (Sel-J) / Oceph (Zuventus) / Omicef (Sel-J) / Omnicef R (Janssen) / Palacef (Renata) / Palcef (Renata) / Rtist (Lupin) / Samnir (Siam Bheasach) / Xi Fu Ni (Central Pharm) / Zefdinir (Zydus) / Zinir (FDC)

Categories

• Anti-Bacterial Agents
• Anti-Infective Agents
• Antibacterials for Systemic Use
• Antiinfectives for Systemic Use
• Aza Compounds
• Azabicyclo Compounds
• beta-Lactams
• Cephalosporins
• Drugs that are Mainly Renally Excreted
• Heterocyclic Compounds, Fused-Ring
• Lactams
• OAT1/SLC22A6 Substrates
• OAT3/SLC22A8 Substrates
• Sulfur Compounds
• Thiazines
• Third-Generation Cephalosporins

UNII

CI0FAO63WC

CAS number

91832-40-5

Weight

Average: 395.414
Monoisotopic: 395.035809931

Chemical Formula

C₁₄H₁₃N₅O₅S₂

InChI Key

RTXOFQZKPXMALH-GHXIOONMSA-N

InChI

InChI=1S/C14H13N5O5S2/c1-2-5-3-25-12-8(11(21)19(12)9(5)13(22)23)17-10(20)7(18-24)6-4-26-14(15)16-6/h2,4,8,12,24H,1,3H2,(H2,15,16)(H,17,20)(H,22,23)/b18-7-/t8-,12-/m1/s1

IUPAC Name

(6R,7R)-7-[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(N-hydroxyimino)acetamido]-3-ethenyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

SMILES

[H][C@]12SCC(C=C)=C(N1C(=O)[C@H]2NC(=O)C(=N/O)\C1=CSC(N)=N1)C(O)=O

Pharmacology

Indication

Cefdinir is indicated to treat acute bacterial otitis media, acute maxillary sinusitis, community-acquired (CA) pneumonia, acute bacterial exacerbations of chronic bronchitis, pharyngitis/tonsillitis, and uncomplicated skin and skin structure infections in children and adults.^14,6

The organisms susceptible to cefdinir have been listed below in addition to their associated clinical condition that may be treated with cefdinir.¹⁴ Various beta-lactamase producing organisms may be treated, as indicated in certain sections below.

Respiratory Acute bacterial exacerbations of chronic bronchitis caused by Haemophilus influenzae, Haemophilus parainfluenzae, Streptococcus pneumoniae (penicillin-susceptible only), and Moraxella catarrhalis

Community-acquired pneumonia caused by Haemophilus influenzae, Haemophilus parainfluenzae, Streptococcus pneumoniae (penicillin-susceptible only), and Moraxella catarrhalis

Ear, nose, and throat Acute bacterial otitis media caused by Haemophilus influenzae, Moraxella catarrhalis, and Streptococcus pneumoniae (penicillin-susceptible only)

Tonsillitis caused by Streptococcus pyogenes

Pharyngitis caused by Streptococcus pyogenes

Acute maxillary sinusitis caused by Haemophilus pneumoniae and Streptococcus pneumoniae (penicillin-susceptible only), and Moraxella catarrhalis

Skin and skin structure infections

Uncomplicated skin and skin structure infections caused by Staphylococcus aureus and Streptococcus pyogenes

Associated Conditions

• Acute Exacerbation of Chronic Bronchitis caused by Haemophilus Influenza
• Acute Exacerbation of Chronic Bronchitis caused by Streptococcus Pneumoniae
• Acute exacerbation of chronic bronchitis caused by Haemophilus parainfluenzae
• Acute exacerbation of chronic bronchitis caused by Moraxella catarrhalis
• Acute maxillary sinusitis caused by H. influenzae
• Acute maxillary sinusitis caused by M. catarrhalis
• Acute maxillary sinusitis caused by Susceptible strains of Streptococcus pneumoniae
• Community acquired pneumonia caused by Susceptible strains of Streptococcus pneumoniae
• Pneumonia due to Haemophilus influenzae (H. influenzae)
• Streptococcal Pharyngitis
• Streptococcal tonsillitis
• Uncomplicated skin and skin structure infections caused by streptococcus pyogenes, staphylococcus aureus
• Acute otitis media caused by M. catarrhalis
• Acute otitis media caused by S.pneumoniae
• Bacterial otitis media caused by Haemophilus influenzae
• Community aquired pneumonia caused by H. parainfluenzae
• Community aquired pneumonia caused by M.catarrhalis

Pharmacodynamics

Cefdinir is a bacteriostatic agent that treats bacterial infections by interfering with cell wall synthesis.¹⁴ Cefdinir exerts broad-spectrum activity against a variety of gram-positive and gram-negative bacterial infections. It is effective against several beta-lactamase enzyme producing bacteria. As a result, many organisms that are resistant to other cephalosporins may be susceptible to cefdinir.^3,4,19

Mechanism of action

Five-member thiazolidine rings that make up penicillins are replaced in cephalosporins by a six-member dihydrothiazine ring, conferring greater bactericidal activity. This This 6-member ring enables cefdinir and other cephalosporins to resist inactivation by certain bacterial enzymes.¹²

With a mechanism similar to other beta-lactam antibiotics, the bactericidal activity of cefdinir is caused by the inhibition of cell wall synthesis via binding to penicillin-binding proteins (PBPs). Cefdinir, like other cephalosporins, penetrates the bacterial cell wall, combats inactivation by beta-lactamase enzymes, and inactivates penicillin-binding proteins.¹² This interferes with the final step of transpeptidation in cell walls, eventually leading to cell lysis, which eventually leads to the death of bacteria that are susceptible to this drug.² Cefdinir has shown affinity to penicillin protein binding proteins 2 and 3. ^7,8,9 It has also been shown to inhibit transpeptidase enzymes of various bacteria, which may play a role in its bactericidal action.^10,11 One in vitro study suggests that cefdinir inhibits myeloperoxidase release extracellularly.¹³ The impact of this potential drug target in relation to its mechanism of action is unknown.

Target	Actions	Organism
APenicillin-binding protein 2	inhibitor	Neisseria gonorrhoeae
APBP3	inhibitor	Haemophilus influenzae
NMyeloperoxidase	inhibitor	Humans
UPeptidoglycan transpeptidase	inhibitor

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Adverse Effects

Comprehensive structured data on known drug adverse effects with statistical prevalence. MedDRA and ICD10 ids are provided for adverse effect conditions and symptoms.

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Contraindications

Structured data covering drug contraindications. Each contraindication describes a scenario in which the drug is not to be used. Includes restrictions on co-administration, contraindicated populations, and more.

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Absorption

Maximal plasma cefdinir concentration can be attained between 2-4 hours after an ingested dose.¹⁴ The bioavailability of cefdinir depends on the formulation used. The estimated bioavailability of cefdinir in the capsule form is approximately 16%-21%, depending on the dose. Absolute bioavailability after the administration of a suspension of cefdinir is 25%.². The Cmax of cefdinir is 1.60 μg/mL after a 300 mg dose with an AUC of 7.05. Cmax is 2.87 μg/mL after a 600 mg dose with an AUC of 11.¹⁴ A meal high in fat can reduce the absorption of cefdinir by up to 15%, however, this is not a cause for clinically significant changes, therefore cefdinir may be taken with or without food.¹⁴ When given with aluminum or magnesium-containing antacids or iron, cefdinir absorption may decrease. It is recommended to allow 2 hours between cefdinir administration and the administration of these agents.²

Volume of distribution

The average volume of distribution of cefdinir in adults is about 0.35 L/kg and 0.67 L/kg in children.^14,20 Another resource estimates the volume of distribution in adults at 1.56–2.09 L/kg.² Cefdinir is found to be distributed in various tissues at clinically effective concentrations. It may be found in the epithelial lining fluid, bronchial mucosa, tonsils, sinuses, skin blister fluid, as well as the middle ear fluid.² Third-generation cephalosporins such as cefdinir cross the blood-brain barrier and are found in high concentrations in the cerebrospinal fluid, unlike their first and second generation counterparts.¹² The wide tissue distribution of cefdinir allows it to treat a variety of infections throughout the body.

Protein binding

The plasma protein binding of cefdinir ranges from 60% to approximately 70%.^2,14

Metabolism

This drug is not significantly metabolized and its pharmacological actions are mainly attributed to the parent drug.^2,14

Route of elimination

This drug is mainly excreted by the kidneys. Dose adjustments may be required for patients with renal impairment or patients on dialysis.¹⁴ Approximately 18.4% of a 300 mg dose of cefdinir was found unchanged in the urine after a 300 mg dose was administered during a pharmacokinetic study of 21 individuals.²⁰ A large proportion of the administered dose is excreted in the feces, although the majority is found in the urine.¹²

Half life

The average plasma elimination half-life is about 1.7 hours in adults.¹⁴ In children and healthy infants, plasma elimination half-life ranges from 1.2–1.5 hours.²

Clearance

The renal clearance in healthy adults in a pharmacokinetic study was 2.0 (± 1.0) mL/min/kg and the clearance in patients with renal failure was lower, decreasing in proportion to the degree of renal impairment.²⁰ Dose adjustment is required in patients with renal impairment.¹⁴

Toxicity

LD50 information Oral LD50 of cefdinir in the rat is >2000 mg/kg.¹⁷

There are limited data regarding cefdinir overdose in the literature. In studies of rodents, one 5600-mg/kg dose administered orally did not lead to adverse effects. Signs of toxicity and overdose caused by other beta-lactam antibiotics included nausea, vomiting, diarrhea, abdominal pain, and seizures.¹⁸

Affected organisms

• Humans and other mammals

Pathways

Not Available

Pharmacogenomic Effects/ADRs

Not Available

Interactions

Drug Interactions

This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.

• All Drugs
• Approved
• Vet approved
• Nutraceutical
• Illicit
• Withdrawn
• Investigational
• Experimental

Drug	Interaction
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(R)-warfarin	The risk or severity of bleeding can be increased when Cefdinir is combined with (R)-warfarin.
(S)-Warfarin	The risk or severity of bleeding can be increased when Cefdinir is combined with (S)-Warfarin.
4-hydroxycoumarin	The risk or severity of bleeding can be increased when Cefdinir is combined with 4-hydroxycoumarin.
Abacavir	Cefdinir may decrease the excretion rate of Abacavir which could result in a higher serum level.
Abciximab	The therapeutic efficacy of Abciximab can be decreased when used in combination with Cefdinir.
Acarbose	Acarbose may decrease the excretion rate of Cefdinir which could result in a higher serum level.
Aceclofenac	Aceclofenac may decrease the excretion rate of Cefdinir which could result in a higher serum level.
Acemetacin	Acemetacin may decrease the excretion rate of Cefdinir which could result in a higher serum level.
Acenocoumarol	The risk or severity of bleeding can be increased when Cefdinir is combined with Acenocoumarol.
Acetaminophen	Acetaminophen may decrease the excretion rate of Cefdinir which could result in a higher serum level.

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Extended description of the mechanism of action and particular properties of each drug interaction.
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Severity
Severity
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Food Interactions

• Avoid taking antacids at same time (up to 2 hours before or after antibiotic).
• Avoid taking iron preparations at same time (up to 2 hours before or after antibiotic).
• Take without regard to meals.

References

Synthesis Reference

Gwan Sun Lee, Young Kil Chang, Jong Pil Chun, Joon Hyung Koh, "Process for preparation of cefdinir." U.S. Patent US6093814, issued December, 1995.

US6093814

General References

1. Kimura Y, Kawamura M, Owada M, Fujiwara T, Maesawa C, Hiramori K: Successful steroid therapy for cefdinir-induced acute tubulointerstitial nephritis with progressive renal failure. Intern Med. 2001 Feb;40(2):114-7. doi: 10.2169/internalmedicine.40.114. [PubMed:11300142]
2. Perry CM, Scott LJ: Cefdinir: a review of its use in the management of mild-to-moderate bacterial infections. Drugs. 2004;64(13):1433-64. doi: 10.2165/00003495-200464130-00004. [PubMed:15212560]
3. Guay DR: Pharmacodynamics and pharmacokinetics of cefdinir, an oral extended spectrum cephalosporin. Pediatr Infect Dis J. 2000 Dec;19(12 Suppl):S141-6. [PubMed:11144395]
4. Paris MM, Devcich KJ: Overview of cefdinir: pharmacokinetics, safety, and efficacy in the treatment of uncomplicated skin and skin structure infections. Cutis. 2004 May;73(5 Suppl):14-8. [PubMed:15182160]
5. Chen J, Ahmad J: Cefdinir-induced hepatotoxicity: potential hazards of inappropriate antibiotic use. J Gen Intern Med. 2008 Nov;23(11):1914-6. doi: 10.1007/s11606-008-0758-y. Epub 2008 Aug 28. [PubMed:18752027]
6. Sader HS, Biedenbach DJ, Streit JM, Jones RN: Cefdinir activity against contemporary North American isolates from community-acquired urinary tract infections. Int J Antimicrob Agents. 2005 Jan;25(1):89-92. doi: 10.1016/j.ijantimicag.2004.07.006. [PubMed:15620832]
7. Ochiai S, Sekiguchi S, Hayashi A, Shimadzu M, Ishiko H, Matsushima-Nishiwaki R, Kozawa O, Yasuda M, Deguchi T: Decreased affinity of mosaic-structure recombinant penicillin-binding protein 2 for oral cephalosporins in Neisseria gonorrhoeae. J Antimicrob Chemother. 2007 Jul;60(1):54-60. Epub 2007 May 31. [PubMed:17540669]
8. Ferrer-Gonzalez E, Kaul M, Parhi AK, LaVoie EJ, Pilch DS: beta-Lactam Antibiotics with a High Affinity for PBP2 Act Synergistically with the FtsZ-Targeting Agent TXA707 against Methicillin-Resistant Staphylococcus aureus. Antimicrob Agents Chemother. 2017 Aug 24;61(9). pii: AAC.00863-17. doi: 10.1128/AAC.00863-17. Print 2017 Sep. [PubMed:28630190]
9. Sanbongi Y, Suzuki T, Osaki Y, Senju N, Ida T, Ubukata K: Molecular evolution of beta-lactam-resistant Haemophilus influenzae: 9-year surveillance of penicillin-binding protein 3 mutations in isolates from Japan. Antimicrob Agents Chemother. 2006 Jul;50(7):2487-92. [PubMed:16801430]
10. Kumar P, Chauhan V, Silva JRA, Lameira J, d'Andrea FB, Li SG, Ginell SL, Freundlich JS, Alves CN, Bailey S, Cohen KA, Lamichhane G: Mycobacterium abscessus l,d-Transpeptidases Are Susceptible to Inactivation by Carbapenems and Cephalosporins but Not Penicillins. Antimicrob Agents Chemother. 2017 Sep 22;61(10). pii: AAC.00866-17. doi: 10.1128/AAC.00866-17. Print 2017 Oct. [PubMed:28760902]
11. Moore BA, Jevons S, Brammer KW: Peptidoglycan transpeptidase inhibition in Pseudomonas aeruginosa and Escherichia coli by Penicillins and Cephalosporins. Antimicrob Agents Chemother. 1979 Apr;15(4):513-7. doi: 10.1128/aac.15.4.513. [PubMed:111613]
12. Prober CG: Cephalosporins: an update. Pediatr Rev. 1998 Apr;19(4):118-27. doi: 10.1542/pir.19-4-118. [PubMed:9557062]
13. Labro MT, el Benna J, Charlier N, Abdelghaffar H, Hakim J: Cefdinir (CI-983), a new oral amino-2-thiazolyl cephalosporin, inhibits human neutrophil myeloperoxidase in the extracellular medium but not the phagolysosome. J Immunol. 1994 Mar 1;152(5):2447-55. [PubMed:8133056]
14. Cefdinir FDA label [Link]
15. MSDS Cefdinir [Link]
16. FDA Label: Apadaz [Link]
17. Pfizer MSDS, Cefdinir [Link]
18. Omnicef [Link]
19. Appropriate prescribing of beta-lactamase antibiotics [Link]
20. Dailymed: Cefdinir capsule [Link]

External Links

Human Metabolome Database

HMDB0014675

KEGG Drug

D00917

KEGG Compound

C08110

PubChem Compound

6915944

PubChem Substance

46505573

ChemSpider

5291705

ChEBI

3485

ChEMBL

CHEMBL927

Therapeutic Targets Database

DAP000436

PharmGKB

PA164768739

RxList

RxList Drug Page

Drugs.com

Drugs.com Drug Page

PDRhealth

PDRhealth Drug Page

Wikipedia

Cefdinir

ATC Codes

J01DD15 — Cefdinir

• J01DD — Third-generation cephalosporins
• J01D — OTHER BETA-LACTAM ANTIBACTERIALS
• J01 — ANTIBACTERIALS FOR SYSTEMIC USE
• J — ANTIINFECTIVES FOR SYSTEMIC USE

MSDS

Download (57 KB)

Clinical Trials

Clinical Trials

Phase	Status	Purpose	Conditions	Count
0	Completed	Treatment	Acute, uncomplicated Appendicitis	1
0	Recruiting	Treatment	Osteomyelitis	1
1	Completed	Not Available	Healthy Volunteers	4
1	Completed	Treatment	Healthy Volunteers	4
2, 3	Completed	Treatment	Acute Otitis Media	1
2, 3	Recruiting	Treatment	Mastitis Acute Female	1
4	Completed	Not Available	Healthy Volunteers	3
4	Completed	Treatment	Acute Bacterial Sinusitis (ABS)	2
4	Completed	Treatment	Acute Otitis Media	2
4	Completed	Treatment	Mild to Moderate Uncomplicated Skin and Skin Structure Infections	1
4	Recruiting	Treatment	Acute Exacerbation of Chronic Bronchitis (AECB) / Community-Acquired Pneumoniae	1
4	Recruiting	Treatment	Antibiotics / Pituitary Adenomas	1
4	Recruiting	Treatment	Pneumonia	1
Not Available	Completed	Treatment	Kwashiorkor / Marasmus	1
Not Available	Completed	Treatment	Snoring / Strep Throat	1

Pharmacoeconomics

Manufacturers

• Aurobindo pharma ltd
• Lupin ltd
• Orchid healthcare
• Sandoz inc
• Teva pharmaceuticals usa
• Abbott laboratories

Packagers

• Abbott Laboratories Ltd.
• A-S Medication Solutions LLC
• Aurobindo Pharma Ltd.
• Ceph International Corp.
• DAVA Pharmaceuticals
• Dispensing Solutions
• Diversified Healthcare Services Inc.
• Greenstone LLC
• Lupin Pharmaceuticals Inc.
• Murfreesboro Pharmaceutical Nursing Supply
• Northstar Rx LLC
• Orchid Healthcare
• PD-Rx Pharmaceuticals Inc.
• Physicians Total Care Inc.
• Redpharm Drug
• Resource Optimization and Innovation LLC
• Sandoz
• Southwood Pharmaceuticals
• Teva Pharmaceutical Industries Ltd.

Dosage forms

Form	Route	Strength
Capsule	Oral	300 mg/1
Powder, for suspension	Oral	125 mg/5mL
Powder, for suspension	Oral	250 mg/5mL

Prices

Unit description	Cost	Unit
Omnicef 125 mg/5ml Suspension 100ml Bottle	101.59USD	bottle
Cefdinir 125 mg/5ml Suspension 60ml Bottle	53.05USD	bottle
Omnicef 300 mg capsule	6.31USD	capsule
Omnicef 300 mg omni-pac capsule	5.72USD	capsule
Cefdinir 300 mg capsule	5.22USD	capsule

DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.

Patents

Patent Number	Pediatric Extension	Approved	Expires (estimated)
Unlock Additional Data
US4935507	No	1990-06-19	2011-12-04

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The date on which a patent was filed with the relevant government.
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Properties

State

Solid

Experimental Properties

Property	Value	Source
melting point (°C)	>135	https://www.trc-canada.com/product-detail/?CatNum=C242670
boiling point (°C)	708.82	https://cymitquimica.com/products/45-1097614/213978-34-8/cefdinir/
water solubility	8.85 ± 0.87 mg/mL	https://www.mdpi.com/1420-3049/22/2/280/htm
logP	-3.47	https://aac.asm.org/content/47/2/689
pKa	9.7	https://www.chemicalbook.com/ChemicalProductProperty_US_CB7483101.aspx

Predicted Properties

Property	Value	Source
Water Solubility	0.0878 mg/mL	ALOGPS
logP	0.02	ALOGPS
logP	-1.7	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	1.74	ChemAxon
pKa (Strongest Basic)	7.45	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	158.21 Å2	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	94.34 m3·mol-1	ChemAxon
Polarizability	36.12 Å3	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted ADMET features

Property	Value	Probability
Human Intestinal Absorption	-	0.7692
Blood Brain Barrier	-	0.9659
Caco-2 permeable	-	0.7205
P-glycoprotein substrate	Non-substrate	0.5185
P-glycoprotein inhibitor I	Non-inhibitor	0.9298
P-glycoprotein inhibitor II	Non-inhibitor	0.9165
Renal organic cation transporter	Non-inhibitor	0.8919
CYP450 2C9 substrate	Non-substrate	0.8676
CYP450 2D6 substrate	Non-substrate	0.8203
CYP450 3A4 substrate	Non-substrate	0.5821
CYP450 1A2 substrate	Non-inhibitor	0.7603
CYP450 2C9 inhibitor	Non-inhibitor	0.8303
CYP450 2D6 inhibitor	Non-inhibitor	0.894
CYP450 2C19 inhibitor	Non-inhibitor	0.8044
CYP450 3A4 inhibitor	Non-inhibitor	0.8436
CYP450 inhibitory promiscuity	Low CYP Inhibitory Promiscuity	0.953
Ames test	Non AMES toxic	0.6686
Carcinogenicity	Non-carcinogens	0.8339
Biodegradation	Not ready biodegradable	0.9925
Rat acute toxicity	1.8801 LD50, mol/kg	Not applicable
hERG inhibition (predictor I)	Weak inhibitor	0.9878
hERG inhibition (predictor II)	Non-inhibitor	0.8964

ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)

Not Available

Spectra

Spectrum	Spectrum Type	Splash Key
Predicted GC-MS Spectrum - GC-MS	Predicted GC-MS	Not Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
LC-MS/MS Spectrum - LC-ESI-qTof , Positive	LC-MS/MS	Not Available
MS/MS Spectrum - , positive	LC-MS/MS	splash10-004i-2983000000-72bf1ac3398fbaa1531b

Taxonomy

Description

This compound belongs to the class of organic compounds known as cephalosporins. These are compounds containing a 1,2-thiazine fused to a 2-azetidinone to for a oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid moiety or a derivative thereof.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Lactams

Sub Class

Beta lactams

Direct Parent

Cephalosporins

Alternative Parents

N-acyl-alpha amino acids and derivatives / 2,4-disubstituted thiazoles / 1,3-thiazines / 2-amino-1,3-thiazoles / Tertiary carboxylic acid amides / Ketoximes / Heteroaromatic compounds / Secondary carboxylic acid amides / Amino acids / AzetidinesThiohemiaminal derivatives / Monocarboxylic acids and derivatives / Dialkylthioethers / Carboxylic acids / Azacyclic compounds / Carbonyl compounds / Hydrocarbon derivatives / Organic oxides / Organopnictogen compounds / Primary amines

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Substituents

Cephalosporin / N-acyl-alpha amino acid or derivatives / Alpha-amino acid or derivatives / 2,4-disubstituted 1,3-thiazole / Meta-thiazine / 1,3-thiazol-2-amine / Azole / Ketoxime / Tertiary carboxylic acid amide / ThiazoleHeteroaromatic compound / Amino acid or derivatives / Secondary carboxylic acid amide / Azetidine / Carboxamide group / Amino acid / Thioether / Azacycle / Dialkylthioether / Hemithioaminal / Monocarboxylic acid or derivatives / Carboxylic acid derivative / Carboxylic acid / Amine / Organic oxide / Organonitrogen compound / Carbonyl group / Organic nitrogen compound / Organooxygen compound / Organic oxygen compound / Primary amine / Hydrocarbon derivative / Organopnictogen compound / Aromatic heteropolycyclic compound

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Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

cephalosporin, ketoxime (CHEBI:3485)

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Drug created on June 13, 2005 07:24 / Updated on November 02, 2019 04:30